Advances in pharmaceutical Co-crystal screening: Effective Co-crystal screening through structural resemblance

Crystal Growth and Design

Volumn 12, Issue 1, 2012, Pages 475-484

  Springuel, Géraldine ^a   Norberg, Bernadette ^b   Robeyns, Koen ^a   Wouters, Johan ^b   Leyssens, Tom ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b UNIVERSITY OF NAMUR   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CO-CRYSTALS; DRIVING FORCES; LEVETIRACETAM; MODEL COMPOUND; MULTI-COMPONENT SYSTEMS; PIRACETAM; SCREENING EFFICIENCY; STRUCTURAL INVESTIGATION;

CRYSTALS; MOLECULES;

COBALT;

EID: 84855404945     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg201291k     Document Type: Article

References (32)

1. Kirwan, D. J.; Orella, C. J. In Handbook of Industrial Crystallization, 2 nd ed.; Myerson, A. S., Ed.; Butterworth-Heinemann: Montvale, MA, 2002; Chapter 11, pp 249-126.
2. Fabbiani, F.; Allan, D.; Parsons, S.; Pulham, C. An exploration of the polymorphism of Piracetam using high pressure CrystEngComm 2005, 7 (29) 179-186 (Pubitemid 40706148)
3. Rodriguez, C.; Bugay, D. E. Characterization of Pharmaceutical Solvates by Combined Thermogravimetric an Infrared Analysis J. Pharm. Sci. 1997, 86 (2) 263-266 (Pubitemid 27078396)
4. Khankari, R. K.; Grant, D. J. W. Pharmaceutical hydrates Thermochim. Acta 1995, 248, 61-79
5. Kumar, V.; Malhotra, S. V. Ionic Liquids as Pharmaceutical Salts: A Historical Perspective ACS Symp. Ser. 2010, 1038, 1-12
6. Neau, S. H. Pharmaceutical Salts Water-Insoluble Drug Formulation 2000, 405-425
7. Sekhon, B. S. Pharmaceutical co-crystals-A review Ars Pharm. 2009, 50 (3) 99-117
8. Vishweshwar, P.; McMahon, J. A.; Bis, J. A.; Zaworotko, M. J. Pharmaceutical co-crystals J. Pharm. Sci. 2006, 95 (3) 499-516
9. Shan, N.; Zaworotko, M. J. The role of co-crystals in pharmaceutical sciances Drug Discovery Today 2008, 13, 440-446
10. Jones, W.; Moetherwell, W. D. S.; Trask, A. V. Pharmaceutical co-crystals: An Emerging approach to physical property enhancement MRS Bull. 2006, 31, 875-879 (Pubitemid 44826643)
11. Cheney, M. L.; Shan, N.; Healey, E. R.; Hanna, M.; Wojtas, L.; Zaworotko, M. J.; Sava, V.; Song, S.; Sanchez-Ramos, J. R. Effects of Crystal Form on Solubility and Pharmacokinetics: A Crystal Engineering Case Study of Lamotrigine Cryst. Growth Des. 2010, 10 (1) 394-405
12. Bauer, J.; Spanton, S.; Henry, R.; Quick, J.; Dziki, W.; Porter, W.; Morris, J. Ritonavir: An Extraordinary Example of Conformational Polymorphism Pharm. Res. 2001, 18 (6) 859-866 (Pubitemid 32783524)
13. Schultheiss, N.; Newman, A. Pharmaceutical Cocrystals and Their Physicochemical Properties Cryst. Growth Des. 2009, 9 (6) 2950-2967
14. Wouters, J.; Quere, L. In Pharmaceutical Salts and Co-crystals; RSC Drug Discovery: Cambridge, 2011.
15. Viertelhaus, S.; Hilfiker, R.; Blatter, F. Piracetam Co-Crystals with OH-Group Functionalized Carboxylic Acids Cryst. Growth Des. 2009, 9 (5) 2220-2228
16. Karki, S.; Friscic, T.; Jones, W.; Motherwell, W. D. S. Screening for Pharmaceutical Cocrystal Hydrates via Neat and Liquid-Assisted Grinding Mol. Pharmaceutics 2007, 4 (3) 347-354 (Pubitemid 46983951)
17. Friscic, T.; Trask, A. V.; Jones, W.; Motherwell, W. D. S. Screening for Inclusion Compounds and Systematic Construction of Three-Component Solids by Liquid-Assisted Grinding Angew. Chem., Int. Ed. 2006, 45, 7546-7550 (Pubitemid 44851678)
18. Zhang, G. G. Z.; Henry, R. F.; Brochardt, T. B.; Lou, X. Efficient Co-crystal Screening Using Solution-Mediated Phase Transformation J. Pharm. Sci. 2007, 96 (5) 990-995 (Pubitemid 46797470)
19. Berry, D. J.; Seaton, C. C.; Clegg, W.; Harrington, R. W.; Coles, S. J.; Horton, P. N.; Hursthouse, M. B.; Storey, R.; Jones, W.; Friscic, T.; Blagden, N. Applying Hot-Stage Microscopy to Co-Crystal Screening: A Study of Nicotinamide with Seven Active Pharmaceutical Ingredients Cryst. Growth Des. 2008, 8 (5) 1697-1712
20. Kenda, B. M.; Matagne, A. C.; Talaga, P. E.; Pasau, P. M.; Differding, E.; Lallemand, B. I.; Frycia, A. M.; Moureau, F. G.; Klitgaard, H. V.; Gillard, M. R.; Fuks, B.; Micel, P. Discovery of 4-Substituted Pyrrolidone Butanamides as New Agents with Significant Antiepileptic Activity J. Med. Chem. 2004, 47, 530-549 (Pubitemid 38129712)
21. Vishweshwar, P.; McMahon, J. A.; Peterson, M. L.; Hickey, M. B.; Shattock, T. R.; Zaworotko, M. J. Crystal engineering of pharmaceutical co-crystals from polymorphic active pharmaceutical ingredients Chem. Commun. 2005, 4601-4603 (Pubitemid 41428459)
22. Liao, X.; Gautam, M.; Grill, A.; Zhu, H. J. Effect of Position Isomerism on the Formation and Physicochemical Properties of Pharmaceutical Co-Crystals J. Pharm. Sci. 2010, 99 (1) 246-254
23. Admiraal, G.; Eikelenboom, J. C.; Vos, A. Structures of the Triclinic and Monoclinic Modifications of (2-Oxo-1-pyrrolidinyl)acetamide Acta Crystallogr. 1982, 38, 2600-2605
24. Sheldrick, M. G. SHELX-97: Program for the Solution of Crystal Structures; University of Göttingen: Göttingen, Germany, 1998.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
26. Etter, M. C.; MacDonald, J. C. Graph-Set Analysis of Hydrogen-Bond Patterns in Organic Crystals Acta Crystallogr. 1990, B46, 256-262
27. Srisanga, S.; ter Horst, J. H. Racemic Compound, Conglomerate, or Solid Solution: Phase Diagram Screening of Chiral Compounds Cryst. Growth Des. 2010, 10 (4) 1808-1812
28. Takata, N.; Shiraki, K.; Takano, R.; Hayashi, Y.; Terada, K. Cocrystal Screening of Stanolone and Mestanolone Using Slurry Crystallization Cryst. Growth Des. 2008, 8 (8) 3032-3037
29. Jayasankar, A.; Reddy, L. S.; Bethune, S. J.; Rodriguez-Hornedo, N. Cryst. Growth Des. 2009, 9, 889-897
30. Nehm, S. J.; Rodriguez-Spong, B.; Rodriguez-Hornedo, N. Cryst. Growth Des. 2006, 6 (2) 592-600
31. Habgood, M.; Price, S. L. Isomers, Conformers, and Cocrystal Stoichiometry: Insights from the Crystal Energy Landscapes of Caffeine with the Hydroxybenzoic Acids Cryst. Growth Des. 2010, 10 (7) 3263-3272
32. Picciochi, R.; Diogo, H. P.; Minas da Piedade, M. E. Thermodynamic characterization of three polymorphic forms of piracetam J. Pharm. Sci. 2011, 100 (2) 594-603